Air-stable and phosphine-free iridium catalysts for highly enantioselective hydrogenation of quinoline derivatives.
Enantioselective hydrogenation of quinoline derivatives catalyzed by phosphine-free chiral cationic Cp*Ir(OTf)(CF 3TsDPEN) complex (CF 3TsDPEN = N-(p-trifluoromethylbenzenesulfonyl)-1,2-diphenylethylene-diamine) afforded the 1,2,3,4-tetrahydroquinoline derivatives in up to 99% ee. The reaction could be carried out with a substrate-to-catalyst molar ratio as high as 1000 in undegassed methanol and with no need for inert gas protection.
Li
Zhi-Wei
ZW
Beijing National Laboratory for Molecular Sciences, Center for Chemical Biology, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
Wang
Tian-Li
TL
He
Yan-Mei
YM
Wang
Zhi-Jian
ZJ
Fan
Qing-Hua
QH
Pan
Jie
J
Xu
Li-Jin
LJ
D000388:Air; D002384:Catalysis; D006865:Hydrogenation; D007495:Iridium / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry; D011804:Quinolines / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D010720:Phosphines; D011804:Quinolines; D007495:Iridium; C037219:quinoline; C044646:phosphine